Bicarbonate Ion → HCID 136127060, compound

HRID 432051Notes

Reaction equation

HRID 432051 reaction equation
[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:13][OH:14])[C:9]([O:11][CH3:12])=[O:10].[C:15](=O)(O)[O-].S(OC)(OC)(=O)=O.O>C(#N)C>[OH:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8](=[N:13][O:14][CH3:15])[C:9]([O:11][CH3:12])=[O:10]

Participants

6

Reactant 4

HCID 769Bicarbonate IonHCID 962WaterHCID 6497Dimethyl SulfateHCID 136388365HCID 136388365, compound

Product 1

HCID 136127060HCID 136127060, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

2.4 g (0.0106 mol) of methyl 2-(2-hydroxyphenyl)-2-hydroxyimino-acetate (Example VII-1a from process step 3; HPLC: 17.1% E, log p=0.95; 68.9% Z, log p=1.68) in 60 ml of acetonitrile are heated under reflux with 1.08 g (0.011 mol) of potassiun bicarbonate and 1.55 g (0.0123 mol) of dimethyl sulphate for 10 hours. The reaction mixture is poured into water and extracted with diethyl ether, and the solvent is distilled off under reduced pressure. This gives 2.1 g of crude product which is chromatographed over silica gel using a mixture of 7 parts of n-hexane and 3 parts of acetone. This gives 1.6 g of product which, according to HPLC, contains 36.9% of methyl Z-2-(2-hydroxyphenyl)-2-methoxyimino-acetate of log p=2.39.

Workup

  1. extractionextracted with diethyl ether
  2. distillationthe solvent is distilled off under reduced pressure
  3. customThis gives 2.1 g of crude product which is chromatographed over silica gel using
  4. additiona mixture of 7 parts of n-hexane and 3 parts of acetone

Sources & evidence

ORD record
ord-e4e138586a8a48c4a2249bdd49f6d329
Source dataset
uspto-grants-2003_12
Patent number
US06660872B1

Reaction notes

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